VARNER, Ark. — The State of Arkansas, dismissing criticism that it intended to rush too many prisoners to their deaths too quickly, on Thursday night carried out its first execution in more than a decade. Using a lethal injection drug that has been the subject of sharp constitutional debate, the state plans to execute three more men by the end of the month, before its supply of the chemical expires.

Ledell Lee, who was condemned to death for the murder of Debra Reese more than 20 years ago in a Little Rock suburb, died at 11:56 p.m. Central time at the Cummins Unit, a prison in southeast Arkansas, after the reprieves he had won in federal and state courts were overturned. He received injections of three drugs: midazolam, to render him unconscious; vecuronium bromide, to halt his breathing; and potassium chloride, to stop his heart.

State officials administered the lethal injection at 11:44 p.m., after Mr. Lee, who requested holy communion as his last meal, wordlessly declined to make a final statement. Sean Murphy, a reporter for The Associated Press who witnessed the execution, said Mr. Lee was not visibly uncomfortable as he was put to death. The prisoner, Mr. Murphy said, was not responsive when the authorities performed consciousness checks.

An evening of appeals kept Mr. Lee, 51, alive as his death warrant neared its midnight expiration. The United States Supreme Court, as well as a federal appeals court in St. Louis, issued temporary stays of execution while they considered his legal arguments. In Little Rock, the Arkansas capital, Gov. Asa Hutchinson monitored developments at the State Capitol.

At one point on Thursday night, the Supreme Court nearly halted Mr. Lee’s execution, but decided, 5 to 4, to allow the state to proceed with its plan, which had called for eight prisoners to be put to death over less than two weeks. The court’s majority — which included the newest justice, Neil M. Gorsuch — did not explain its decision, but in a dissent, Justice Stephen G. Breyer complained about how the state had established its execution schedule because of the approaching expiration date of Arkansas’s stock of midazolam.

Solomon Graves, a spokesman for the Arkansas Department of Correction, waited for news from the death chamber at the Cummins Unit prison on Thursday.
Kelly P. Kissel/Associated Press

“In my view, that factor, when considered as a determining factor separating those who live from those who die, is close to random,” Justice Breyer wrote. “I have previously noted the arbitrariness with which executions are carried out in this country. The cases now before us reinforce that point.”

Through his lawyers, who raised concerns about his intellectual capacity and the personal conduct and conflicts of some people who were involved in his trial, Mr. Lee maintained his innocence, and a state judge’s ruling threatened to block the state from using one of its execution drugs.

But the courts ultimately allowed his death sentence to be carried out, making him the first prisoner in Arkansas to be executed since 2005. He had been sentenced to death in 1995 after a jury found that he had murdered Ms. Reese with a tire thumper in Jacksonville. In a 1997 ruling that upheld the conviction, the Arkansas Supreme Court said Mr. Lee had struck Ms. Reese 36 times with the small bat-shaped tool, which her husband had given her for protection.

The Arkansas Parole Board said this month that Mr. Lee’s plea for executive clemency was “without merit,” and this week, the courts repeatedly rebuffed arguments to, at the least, delay his execution.

“Arkansas’s decision to rush through the execution of Mr. Lee just because its supply of lethal drugs are expiring at the end of the month denied him the opportunity to conduct DNA testing that could have proven his innocence,” Nina Morrison, one of Mr. Lee’s lawyers, said in a statement. “While reasonable people can disagree on whether death is an appropriate form of punishment, no one should be executed when there is a possibility that person is innocent.”

As Mr. Lee’s lawyers spent Thursday urging the courts to spare his life, the cascade of legal developments did not affect the stay of execution that another inmate, Stacey E. Johnson, received on Wednesday evening, about 24 hours before he was scheduled to be put to death.

Mr. Johnson has also claimed innocence, and the State Supreme Court’s decision will allow for new forensic testing of some evidence. He was convicted of the 1993 rape and murder of Carol Heath, whose two children, according to the state, “were left alone overnight with their mother’s lifeless body.”

Some of the most pitched legal clashes surrounding Arkansas’s planned executions centered on the state’s execution drugs, including midazolam, a common sedative that has been used in executions in the United States since 2013.

The drug was conceived decades ago as an alternative to Valium, and it grew in popularity to become one of the world’s essential drugs, a pharmaceutical staple for procedures like colonoscopies. But as states struggled to obtain drugs for executions, they began to turn to midazolam, which has also been known as Versed, as a way to render prisoners unconscious before infusions of other drugs that cause excruciating suffering.

Most executions involving midazolam have gone as planned. But a handful — in Alabama, Arizona, Ohio and Oklahoma — were criticized as botched, and some opponents argued that the drug had not sedated prisoners enough to allow them to die painless deaths. In 2015, the United States Supreme Court upheld the use of midazolam as an execution drug, but its future has remained a subject of deep dispute that has bounced among the nation’s trial and appellate courts.

Arkansas was merely the latest stage for a debate that has centered on the Eighth Amendment’s protections against cruel and unusual punishment. A Federal District Court judge in Little Rock moved on Saturday to block the Arkansas executions because of her concerns about midazolam. That decision was later overturned.

But the state also faced resistance in the courts because of how it purchased the second of its lethal injection drugs, vecuronium bromide. The nation’s largest pharmaceutical distributor, McKesson Corporation, accused the state of deceiving it as part of an end-run around restrictions on the sales of drugs that can be used in lethal injections.

According to the company, the Arkansas Department of Correction did not disclose its intent for the drug, which the state had struggled to purchase elsewhere. The inadvertent sale, the company said, was improper, and it demanded that Arkansas return the drug.

Judge Alice Gray of Circuit Court in Little Rock issued an order blocking the state from using the drug, effectively staying the executions. The state, which denied wrongdoing, appealed to the Arkansas Supreme Court on Thursday.

“No valid legal theory supports McKesson’s argument that a person who purchases a product must use that product in a certain way as dictated by the seller after the completion of the transaction, or must return the product on demand by the seller after the completion of the transaction,” lawyers for the state wrote in their appeal.

The State Supreme Court agreed with the attorney general’s office on Thursday evening and lifted Judge Gray’s order, allowing prison officials to use the drug it bought from McKesson last summer.

Mr. Lee’s execution prompted immediate criticism.

“Today is a shameful day for Arkansas, which is callously rushing the judicial process by treating human beings as though they have a sell-by date,” Amnesty International said in a statement. “While other states have increasingly come to the conclusion that the capital punishment system is beyond repair, Arkansas is running in the opposite direction from progress. This assembly line of executions must stop, and this cruel and inhuman punishment should be ended once and for all.”

But Arkansas officials cast the execution as a milestone.

“Tonight, the lawful sentence of a jury which has been upheld by the courts through decades of challenges has been carried out,” the Arkansas attorney general, Leslie Rutledge, said in a statement. “The family of the late Debra Reese, who was brutally murdered with a tire thumper after being targeted because she was home alone, has waited more than 24 years to see justice done. I pray this lawful execution helps bring closure for the Reese family.”

Speaking at the prison, Mr. Hutchinson’s spokesman, J. R. Davis, said, “It’s a moment of reflection, but at the end of the night, the right thing was done.”

For breaking news and in-depth reporting, follow @NYTNational on Twitter.